Composition and method for controlling plant diseases

ABSTRACT

The present invention provides a composition for controlling plant diseases having an excellent control efficacy on plant diseases. A composition for controlling plant diseases comprising a carboxylic acid compound represented by a formula (I): wherein each of symbols are the same as defined in the Description; or salts thereof and one or more kinds of azole compounds selected from the group (A) consisting of tebuconazole, difenoconazole, triticonazole, imazalil, triadimenol, fluquinconazole, prochloraz, prothioconazole, diniconazole, diniconazole M, cyproconazole, tetraconazole, ipconazole, triforine, pyrifenox, fenarimol, nuarimol, oxpoconazole fumarate, pefurazoate, triflumizole, azaconazole, bitertanol, bromuconazole, epoxiconazole, fenbuconazole, flusilazole, flutriafol, hexaconazole, imibenconazole, myclobutanil, penconazole, propiconazole, simeconazole, triadimefon and met conazole, shows an excellent controlling efficacy on plant diseases.

TECHNICAL FIELD

The present invention relates to a composition for controlling plantdiseases and a method for controlling plant diseases.

BACKGROUND ART

Hitherto, many compounds have been known as active ingredients in acomposition for controlling plant diseases (The Pesticide Manual-15thedition, published by British Crop Protection Council (BCPC),ISBN978-1-901396-18-8).

DISCLOSURE OF INVENTION Problems to be Solved by Invention

An object of the present invention is to provide a composition forcontrolling plant diseases having an excellent control efficacy on plantdiseases.

Means to Solve Problems

The present inventors have intensively studied to find out a compositionfor controlling plant diseases having an excellent control efficacy onplant diseases. As a result, they have found that a compositioncomprising a carboxylic acid compound represented by the followingformula (I) or salts thereof and one or more kinds of azole compoundsselected from the group consisting of the following group (A) has anexcellent controlling effect on plant diseases. Thus, the presentinvention has been completed.

Specifically, the present invention includes:

[1] A composition for controlling plant diseases comprising a carboxylicacid compound represented by a formula (I):

wherein

n represents an integer selected from 1 to 5;

R¹ represents a halogen atom, a hydroxy group, a nitro group, a C1-C6alkyl group or a C1-C6 alkoxy group; and

when n represents an integer selected from 2 to 5, each R¹ may be thesame or different; or salts thereof and

at least one kind of azole compounds selected from the group (A)consisting of tebuconazole, difenoconazole, triticonazole, imazalil,triadimenol, fluquinconazole, prochloraz, prothioconazole, diniconazole,diniconazole M, cyproconazole, tetraconazole, ipconazole, triforine,pyrifenox, fenarimol, nuarimol, oxpoconazole fumarate, pefurazoate,triflumizole, azaconazole, bitertanol, bromuconazole, epoxiconazole,fenbuconazole, flusilazole, flutriafol, hexaconazole, imibenconazole,myclobutanil, penconazole, propiconazole, simeconazole, triadimefon andmetconazole.

[2] The composition for controlling plant diseases according to [1]wherein a weight ratio of the carboxylic acid compound or salts thereofto the azole compounds is in the range of 100:1 to 1:100.

[3] The composition for controlling plant diseases according to [1]wherein at least one kind of azole compounds is selected from the group(A) consisting of tebuconazole, difenoconazole, triticonazole, imazalil,triadimenol, fluquinconazole, prochloraz, prothioconazole, diniconazole,diniconazole M, cyproconazole, tetraconazole, ipconazole, triforine,pyrifenox, fenarimol, nuarimol, oxpoconazole fumarate, pefurazoate,triflumizole, azaconazole, bitertanol, bromuconazole, epoxiconazole,fenbuconazole, flusilazole, flutriafol, hexaconazole, imibenconazole,myclobutanil, penconazole, propiconazole, simeconazole and triadimefon.

[4] The composition for controlling plant diseases according to [3]wherein a weight ratio of the carboxylic acid compound or salts thereofto the azole compounds is in the range of 100:1 to 1:100.

[5] A method for controlling plant diseases which comprises applying aneffective amount of the composition for controlling plant diseasesaccording to [1] or [2] to a plant or a soil for cultivating the plant.

[6] A method for controlling plant diseases which comprises applying aneffective amount of the composition for controlling plant diseasesaccording to [1] or [2] plant seeds.

[7] The method for controlling plant diseases according to [6] whereinthe plant seeds are seeds of corn, cotton, soybean, beet, rapeseed,wheat or rice.

[8] A method for controlling plant diseases which comprises applying aneffective amount of the composition for controlling plant diseasesaccording to [3] or [4] to a plant or a soil for cultivating the plant.

[9] A method for controlling plant diseases which comprises applying aneffective amount of the composition for controlling plant diseasesaccording to [3] or [4] to plant seeds.

[10] The method for controlling plant diseases according to [9] whereinthe plant seeds are seeds of corn, cotton, soybean, beet, rapeseed,wheat or rice.

Effect of Invention

The present invention can control plant diseases.

MODE FOR CARRYING OUT THE INVENTION

Hereinafter, the present invention is explained in detail.

The term “composition for controlling plant diseases of the presentinvention” refers to a composition comprising a carboxylic acid compoundrepresented by a formula (I):

wherein

n represents an integer selected from 1 to 5;

R¹ represents a halogen atom, a hydroxy group, a nitro group, a C1-C6alkyl group or a C1-C6 alkoxy group; and

when n represents an integer selected from 2 to 5, each R¹ may be thesame or different (hereinafter referred as to “the present carboxylicacid compound”); or salts thereof and

at least one kind of azole compounds selected from the group (A)consisting of tebuconazole, difenoconazole, triticonazole, imazalil,triadimenol, fluquinconazole, prochloraz, prothioconazole, diniconazole,diniconazole M, cyproconazole, tetraconazole, ipconazole, triforine,pyrifenox, fenarimol, nuarimol, oxpoconazole fumarate, pefurazoate,triflumizole, azaconazole, bitertanol, bromuconazole, epoxiconazole,fenbuconazole, flusilazole, flutriafol, hexaconazole, imibenconazole,myclobutanil, penconazole, propiconazole, simeconazole, triadimefon andmetconazole (hereinafter referred as to “the present azole compounds”).

In the formula (I), as the group represented by the R¹,

the term “halogen atom” includes, for example, a fluorine atom, achlorine atom, a bromine atom and an iodine atom;

the term “C1-C6 alkyl group” includes, for example, a methyl group, anethyl group, a propyl group, a butyl group, a pentyl group, a hexylgroup, a 1-methylethyl group, a 2-methylpropyl group, a 3-methylbutylgroup and a 4-methylpentyl group;

the term “C1-C6 alkoxy group” includes, for example, a methoxy group, anethoxy group, a propoxy group, a butoxy group, a pentyloxy group, ahexyloxy group, a 1-methylethoxy group, a 2-methylpropoxy group, a3-methylbutoxy group and a 4-methylpentyloxy group.

The salts of the present carboxylic acid compound include, for example,inorganic base salts and organic base salts.

The inorganic base salts include, for example, alkali metal salts suchas sodium salts and potassium salts, alkaline-earth metal salts such ascalcium salts and magnesium salts, and ammonium salts.

The organic base salts include, for example, amine salts such astriethylamine salts, pyridine salts, picoline salts, ethanolamine salts,triethanolamine salts, dicyclohexylamine salts, andN,N′-dibenzylethylenediamine salts.

Examples of the present carboxylic acid compound include as follows:

the carboxylic acid compound represented by formula (I) wherein n is 1,and R¹ is a methyl group, a methoxy group, a nitro group, or a halogenatom; and

the carboxylic acid compound represented by formula (I) wherein n is 2,R¹ is a C1-C2 alkyl group or a halogen atom, and each R¹ may be the sameor different.

Next, specific examples of the present carboxylic acid compound areshown below.

The carboxylic acid compound represented by the formula (I-a):

wherein a combination of n and R¹ represents any combination as shown inTable 1.

TABLE 1 Compound No. n R¹ 1 1 4-CH₃ — 2 1 4-CH₃O — 3 1 4-F — 4 1 4-Cl —5 1 4-Br — 6 1 4-I — 7 1 4-NO₂ — 8 1 2-Cl — 9 2 3-Cl 4-Cl

In Table 1, the “4-” in the substituent “4-CH₃” etc. of R¹ means thatsuch substituent is present as R¹ at the 4-position of the benzene ringin the above formula (I-a).

The present carboxylic acid compounds are those described in, forexample, JP-11-255607 A and JP-2001-139405 A, and can be prepared, forexample, according to the methods described therein.

Also, tebuconazole, difenoconazole, triticonazole, imazalil,triadimenol, fluquinconazole, prochloraz, prothioconazole, diniconazole,diniconazole M, cyproconazole, tetraconazole, ipconazole, triforine,pyrifenox, fenarimol, nuarimol, oxpoconazole fumarate, pefurazoate,triflumizole, azaconazole, bitertanol, bromuconazole, epoxiconazole,fenbuconazole, flusilazole, flutriafol, hexaconazole, imibenconazole,myclobutanil, penconazole, propiconazole, simeconazole, triadimefon andmetconazole that are used in the present invention are all knowncompounds, and are described in, for example, “The PESTICIDE MANUAL—15thEDITION (BCPC published) ISBN 978-1-901396-18-8”, pages 1072, 354, 1182,629, 1147, 543, 928, 965, 384, 384, 287, 1096, 663, 1177, 1255, 465,1250, 854, 868, 1171, 52, 116, 134, 429, 468, 554, 560, 611, 643, 801,869, 952, 1033, 1145 and 749 respectively.

These compounds are either commercially available, or can be prepared byknown methods.

Tebuconazole, difenoconazole, triticonazole, imazalil, triadimenol,fluquinconazole, prochloraz, prothioconazole, diniconazole, diniconazoleM, cyproconazole, tetraconazole, ipconazole, triforine, pyrifenox,fenarimol, nuarimol, oxpoconazole fumarate, pefurazoate, triflumizole,azaconazole, bitertanol, bromuconazole, epoxiconazole, fenbuconazole,flusilazole, flutriafol, hexaconazole, imibenconazole, myclobutanil,penconazole, propiconazole, simeconazole, triadimefon and metconazolethat are used in the present invention are fungicidal compounds thatknown as demethylation inhibitor (abbreviation: DMI agent).

The weight ratio of the present carboxylic acid compound or saltsthereof to the present azole compounds in the composition forcontrolling plant diseases of the present invention includes, but is notlimited to, in the range of usually 2 to 10,000,000 parts by weight andpreferably 10 to 100,000 parts by weight of the present azole compoundsopposed to 1,000 parts by weight of the present carboxylic acid compoundor salts thereof.

Although the composition for controlling plant diseases of the presentinvention may be a mixture as itself of the present carboxylic acidcompound or salts thereof and the present azole compounds, thecomposition of the present invention is usually prepared by mixing thepresent carboxylic acid compound or salts thereof, the present azolecompounds and an inert carrier, and if necessary, adding a surfactant orother pharmaceutical additives, and then formulating into the form ofoil solution, emulsifiable concentrate, flowable formulation, wettablepowder, granulated wettable powder, dust formulation, granules and soon.

Also the composition for controlling plant diseases formulated asaforementioned can be used by itself or with an addition of an inertcarrier as an agent for controlling plant diseases.

In the composition for controlling plant diseases of the presentinvention, a total amount of the present carboxylic acid compound orsalts thereof and the present azole compounds is in the range of usually0.1% to 99% by weight, preferably 0.2% to 90% by weight, and morepreferably 1% to 80% by weight.

Also the composition for controlling plant diseases of the presentinvention may further optionally contain one or more pesticides and/orfungicides other than those mentioned above.

Examples of the inert carrier used in the formulation include an inertsolid carrier and an inert liquid carrier.

Examples of the solid carrier used in the formulation includefinely-divided powder or particles consisting of minerals (for example,kaolin clay, attapulgite clay, bentonite, montmorillonite, acid clay,pyrophyllite, talc, diatomaceous earth, or calcite), natural organicsubstances (for example, corncob powder, or walnut shell powder),synthetic organic substances (for example, urea), salts (for example,calcium carbonate, or ammonium sulfate), synthetic inorganic substances(for example, synthetic hydrous silicon oxide) and the others. Examplesof the liquid carrier include aromatic hydrocarbons (for example,xylene, alkyl benzene, or methylnaphtalene), alcohols (for example,2-propanol, ethylene glycol, propylene glycol, or ethylene glycolmonoethyl ether), ketones (for example, acetone, cyclohexanone, orisophorone), vegetable oils (for example, soybean oil, or cotton oils),petroleum-derived aliphatic hydrocarbons, esters, dimethylsulfoxide,acetonitrile and water.

Examples of the surfactant include anionic surfactant (for example,alkyl sulfate salts, alkylaryl sulfate salts, dialkyl sulfosuccinatesalts, polyoxyethylene alkylaryl ether phosphates, lignin sulfonate, ornaphthalenesulfonate formaldehyde polycondensation), nonionic surfactant(for example, polyoxyethylene alkylaryl ether, polyoxyethylene alkylpolyoxypropylene block copolymer, or sorbitan fatty acid ester) andcationic surfactant (for example, alkyltrimethyl ammonium salts).

Examples of the other pharmaceutical additives include water-solublepolymer (for example, polyvinyl alcohol, or polyvinyl pyrrolidone),polysaccharides (for example, arabic gum, alginic acid and saltsthereof, CMC (carboxymethyl-cellulose), or xanthan gum), inorganicsubstances (for example, aluminum magnesium silicate, or alumina-sol),antiseptic agent, coloring agent, and stabilizing agent (for example,BHT, or PAP (isopropyl acid phosphate)).

The composition for controlling plant diseases of the present inventionis used to control a plant disease by applying it to a plant or a soilfor cultivating the plant.

The plant diseases which can be controlled by the present invention areexemplified below:

Rice diseases: blast (Magnaporthe oryzae) helminthosporium leaf spot(Cochliobolus miyabeanus) and bakanae disease (Gibberella fujikuroi);

Diseases of barley, wheat, oats and rye: powdery mildew (Erysiphegraminis), Fusarium head blight (Fusarium graminearum, F. avenaceum, F.culmorum, F. asiaticum, Microdochium nivale), rust (Pucciniastriiformis, P. graminis, P. recondita, P. hordei), snow blight (Typhulasp., Micronectriella nivalis), loose smut (Ustilago tritici, U. nuda)bunt (Tilletia caries), eyespot (Pseudocercosporella herpotrichoides)scald (Rhynchosporium secalis), leaf blotch (Septoria tritici), glumeblotch (Leptosphaeria nodorum) and net blotch (Pyrenophora teresDrechsler);

Citrus diseases: melanose (Diaporthe citri) and scab (Elsinoe fawcetti);

Apple diseases: blossom blight (Monilinia mali), canker (Valsaceratosperma), powdery mildew (Podosphaera leucotricha), Alternaria leafspot (Alternaria alternata apple pathotype), scab (Venturia inaequalis)and bitter rot (Colletotrichum acutatum);

Pear diseases: scab (Venturia nashicola, V. pirina), black spot(Alternaria alternata Japanese pear pathotype) and rust (Gymnosporangiumharaeanum)

Peach diseases: brown rot (Monilinia fructicola), scab (Cladosporiumcarpophilum) and Phomopsis rot (Phomopsis sp.);

Grapes diseases: anthracnose (Elsinoe ampelina), ripe rot (Glomerellacingulata), powdery mildew (Uncinula necator), rust (Phakopsoraampelopsidis), black rot (Guignardia bidwellii) and gray mold (Botrytiscinerea);

Diseases of Japanese persimmon: anthracnose (Gloeosporium kaki) and leafspot (Cercospora kaki, Mycosphaerella nawae);

Diseases of gourd family: anthracnose (Colletotrichum lagenarium),powdery mildew (Sphaerotheca fuliginea) gummy stem blight(Mycosphaerella melonis) and Fusarium wilt (Fusarium oxysporum);

Tomato diseases: early blight (Alternaria solani) and leaf mold(Cladosporium fulvum);

Egg plant disease: brown spot (Phomopsis vexans) and powdery mildew(Erysiphe cichoracearum);

Diseases of Cruciferous Vegetables: Alternaria leaf spot (Alternariajaponica) and white spot (Cercosporella brassicae);

Rapeseed diseases: Sclerotinia rot (Sclerotinia sclerotiorum), blackspot (Alternaria brassicae), powdery mildew (Erysiphe cichoracearum),blackleg (Leptosphaeria maculans);

Welsh onion diseases: rust (Puccinia allii);

Soybean diseases: purple seed stain (Cercospora kikuchii), sphacelomascad (Elsinoe glycines), pod and stem blight (Diaporthe phaseolorum var.sojae) and rust (Phakopsora pachyrhizi);

Adzuki-bean diseases: gray mold (Botrytis cinerea), sclerotinia rot(Sclerotinia sclerotiorum);

Kidney bean diseases: gray mold (Botrytis cinerea), Sclerotinia rot(Sclerotinia sclerotiorum) anthracnose (Colletotrichum lindemthianum);

Peanut diseases: leaf spot (Cercospora personata) brown leaf spot(Cercospora arachidicola) and southern blight (Sclerotium rolfsii);

Garden pea diseases: powdery mildew (Erysiphe pisi);

Strawberry diseases: powdery mildew (Sphaerotheca humuli);

Tea diseases: net blister blight (Exobasidium reticulatum) white scab(Elsinoe leucospila), gray blight (Pestalotiopsis sp.) and anthracnose(Colletotrichum theae-sinensis);

Cotton diseases: Fusarium wilt (Fusarium oxysporum), damping-off(Rhizoctonia solani);

Tabacco diseases: brown spot (Alternaria longipes), powdery mildew(Erysiphe cichoracearum) and anthracnose (Colletotrichum tabacum);

Sugar beet diseases: cercospora leaf spot (Cercospora beticola), leafblight (Thanatephorus cucumeris) and root rot (Thanatephorus cucumeris);

Rose diseases: black spot (Diplocarpon rosae) and powdery mildew(Sphaerotheca pannosa)

Chrysanthemum diseases: leaf blight (Septoria chrysanthemi-indici) andwhite rust (Puccinia horiana);

Various plants diseases: gray mold (Botrytis cinerea) Sclerotinia rot(Sclerotinia sclerotiorum)

Japanese radish Disease: Alternaria leaf spot (Alternaria brassicicola);

Turfgrass diseases: dollar spot (Sclerotinia homeocarpa), brown patchand large patch (Rhizoctonia solani); and

Banana diseases: Sigatoka disease (Mycosphaerella fijiensis,Mycosphaerella musicola, Pseudocercospora musae).

The composition for controlling plant diseases of the present inventioncan be used in agricultural lands such as fields, paddy fields, drypaddy fields, lawns and orchards or in non-agricultural lands. Also thecomposition for controlling plant diseases of the present invention cancontrol plant diseases in agricultural lands and the others forcultivating the following “plant” and the others.

The plant which can be applied by the composition for controlling plantdiseases of the present invention is exemplified below:

Crops:

corn, rice, wheat, barley, rye, oat, sorghum, cotton, soybean, peanut,buckwheat, beet, rapeseed, sunflower, sugar cane, tobacco, and theothers;

Vegetables:

solanaceous vegetables (for example, eggplant, tomato, pimento, pepperand potato),cucurbitaceous vegetables (for example, cucumber, pumpkin, zucchini,water melon and melon),cruciferous vegetables (for example, Japanese radish, white turnip,horseradish, kohlrabi, Chinese cabbage, cabbage, leaf mustard, broccoli,cauliflower, colza),asteraceous vegetables (for example, burdock, crown daisy, artichoke andlettuce),liliaceous vegetables (for example, green onion, onion, garlic andasparagus),ammiaceous vegetables (for example, carrot, parsley, celery andparsnip),chenopodiaceous vegetables (for example, spinach and Swiss chard),lamiaceous vegetables (for example, Perilla frutescens, mint and basil),strawberry, sweet potato, Dioscorea japonica, colocasia and the others;

Fruits:

pomaceous fruits (for example, apple, pear, Japanese pear, Chinesequince and quince),stone fleshy fruits (for example, peach, plum, nectarine, Prunus mume,cherry fruit, apricot and prune),citrus fruits (for example, Citrus unshiu, orange, lemon, lime andgrapefruit),nuts (for example, chestnut, walnuts, hazelnuts, almond, pistachio,cashew nuts and macadamia nuts),berry fruits (for example, blueberry, cranberry, blackberry andraspberry),grape, kaki persimmon, olive, Japanese plum, banana, coffee, date palm,coconuts, oil palm and the others;

Trees other than fruit trees:

tea, mulberry,flowering plant (for example, dwarf azalea, camellia, hydrangea,sasanqua, Illicium anisatum, cherry trees, tulip tree, crape myrtle andfragrant olive),roadside trees (for example, ash, birch, dogwood, Eucalyptus, Ginkgobiloba, lilac, maple, Quercus, poplar, Judas tree, Liquidambarformosana, plane tree, zelkova, Japanese arborvitae, fir wood, hemlock,juniper, Pinus, Picea, Taxus cuspidate, elm and Japanese horsechestnut), Sweet viburnum, Podocarpus macrophyllus, Japanese cedar,Japanese cypress, croton, Japanese spindletree and Photinia glabra;

Lawn:

sods (for example, Zoysia japonica, Zoysia matrella), bermudagrasses(for example, Cynodon dactylon),bent glasses (for example, Agrostis gigantea, Agrostis stolonifera,Agrostis capillaris),blueglasses (for example, Poa pratensis, Poa trivialis), festucae (forexample, Festuca arundinacea Schreb., Festuca rubra L. var. commutataGaud., Festuca rubra L. var. genuina Hack),ryegrassses (for example, Lolium multiflorum Lam, Lolium perenne L),Dactylis glomerata, Phleum pratense;

Others:

flowers (for example, rose, carnatidn, chrysanthemum, Eustoma,gypsophila, gerbera, marigold, salvia, petunia, verbena, tulip, aster,gentian, lily, pansy, cyclamen, orchid, lily of the valley, lavender,stock, ornamental cabbage, primula, poinsettia, gladiolus, cattleya,daisy, cymbidium and begonia),bio-fuel plants (for example, jatropha, safflower, Camelina, switchgrass, Miscanthus giganteus, Phalaris arundinacea, Arundo donax, kenaf,cassava, willow), and ornamental foliage plants, and the others.

Among the above-mentioned plants, preferred examples include corn, beet,rice, sorghum, soybean, cotton, rapeseed and wheat.

The above-mentioned “plant” includes plants, to which a resistance hasbeen conferred by a classical breeding method or genetic engineeringtechnique.

The composition for controlling plant diseases of the present inventionis used to control plant diseases by applying it to the plant or an areafor cultivating the plant. Such plants to be used herein includefoliages of plant, flowers of plant, fruits of plant, seeds of plant, orbulbs of plant. The bulbs to be used herein are intended to mean bulb,corm, rootstock, tubera, tuberous root and rhizophore.

The method for controlling plant diseases of the present inventioncomprises applying the composition for controlling plant diseases of thepresent invention.

Specific examples of the method of applying the composition forcontrolling plant diseases of the present invention include anapplication to stems and leaves of plants such as a foliage application;an application to seeds of plants; and an application to area forcultivating plants such as a soil treatment and a submerged application.

Specific examples of the application to stems and leaves of plants suchas a foliage application in the present invention include an applicationto surfaces of plants to be cultivated, for example, by a groundapplication with a manual sprayer, a power sprayer, a boom sprayer orPancle sprayer or by an aerial application by using manned or unmannedairplane or helicopter.

Specific examples of the application to seeds of plants in the presentinvention include an application of the composition for controllingplant diseases of the present invention to seeds or bulbs of plants,more specifically, a spray coating treatment on the surface of seeds orbulbs, a. smear treatment on the seeds or bulbs of plants, an immersiontreatment, a film coating treatment and a pellet coating treatment.

Specific examples of the application to area for cultivating plants suchas a soil application and submerged application in the present inventioninclude, a planting hole application, a plant foot application, a rowapplication, an in-furrow application, an overall application, a sideditch application, a nursery box application, a nursery bed application,a nursery soil incorporation, a bed soil incorporation, a pastefertilizer incorporation, a paddy water application, and a submergedapplication under flooding condition.

When the composition for controlling plant diseases of the presentinvention is applied to plants or area for cultivating plants, theapplication dose varies depending on the kinds of plants to beprotected, the species or the degree of emergence of plant diseases tobe controlled, the dosage form, the timing of application, weatherconditions, etc., but the total amount of the present carboxylic acidcompound or salt thereof and the azole compounds is in the range ofusually from 0.05 to 10,000 g, preferably from 0.5 to 1,000 g per 1,000m² of the area for cultivating plants.

When the composition for controlling plant diseases of the presentinvention is applied to seeds of plants, the application dose variesdepending on the kinds of plants to be protected, the species or thedegree of emergence of plant diseases to be controlled, the dosage form,the timing of application, weather conditions, etc., but the totalamount of the present carboxylic acid compound or salts thereof and theazole compounds is in the range of usually from 0.001 to 100 g,preferably from 0.05 to 50 g per 1 kg of the seeds.

The emulsifiable concentrate, the wettable powder or the flowableformulation, etc. of the composition for controlling plant diseases ofthe present invention is usually applied by diluting it with water, andthen spreading it. In this case, the total concentration of the presentcarboxylic acid compound or salts thereof and the azole compounds is inthe range of usually 0.00001 to 10% by weight, and preferably 0.0001 to5% by weight. The dust formulation or the granular formulation, etc, isusually applied as itself without diluting it.

EXAMPLES

The following Examples including Formulation examples and Test examplesserve to illustrate the present invention in more detail, which shouldnot intend to limit the present invention. In the Examples, the term“part(s)” means part(s) by weight unless otherwise specified, and “thepresent carboxylic acid compound (Compound No. X)” corresponds to“Compound No. X” listed in Table 1, that is, for example, “the presentcarboxylic acid compound (Compound No. 4)” refers to Compound No. 4listed in Table 1.

Formulation examples are shown below.

Formulation Example 1

Ten (10) parts of the present carboxylic acid compound selected fromCompound No. 1 to Compound No. 9, 1 part of tebuconazole, 35 parts of amixture (weight ratio 1:1) of white carbon and ammonium polyoxyethylenealkyl ether sulfate are mixed with an appropriate amount of water so asto give a total amount of 100 parts, and then the mixture isfinely-ground by a wet grinding method to obtain a flowable formulation.

Formulation Example 2

Ten (10) parts of the present carboxylic acid compound selected fromCompound No. 1 to Compound No. 9, 1 part of difenoconazole, 35 parts ofa mixture (weight ratio 1:1) of white carbon and ammoniumpolyoxyethylene alkyl ether sulfate are mixed with an appropriate amountof water so as to give a total amount of 100 parts, and then the mixtureis finely-ground by a wet grinding method to obtain a flowableformulation.

Formulation Example 3

Ten (10) parts of the present carboxylic acid compound selected fromCompound No. 1 to Compound No. 9, 1 part of triadimenol, 35 parts of amixture (weight ratio 1:1) of white carbon and ammonium polyoxyethylenealkyl ether sulfate are mixed with an appropriate amount of water so asto give a total amount of 100 parts, and then the mixture isfinely-ground by a wet grinding method to obtain a flowable formulation.

Formulation Example 4

Ten (10) parts of the present carboxylic acid compound selected fromCompound No 1 to Compound No. 9, 1 part of prothioconazol, 35 parts of amixture (weight ratio 1:1) of white carbon and ammonium polyoxyethylenealkyl ether sulfate are mixed with an appropriate amount of water so asto give a total amount of 100 parts, and then the mixture isfinely-ground by a wet grinding method to obtain a flowable formulation.

Formulation Example 5

Ten (10) parts of the present carboxylic acid compound selected fromCompound No. 1 to Compound No. 9, 1 part of triticonazole, 35 parts of amixture (weight ratio 1:1) of white carbon and ammonium polyoxyethylenealkyl ether sulfate are mixed with an appropriate amount of water so asto give a total amount of 100 parts, and then the mixture isfinely-ground by a wet grinding method to obtain a flowable formulation.

Formulation Example 6

Ten (10) parts of the present carboxylic acid compound selected fromCompound No. 1 to Compound No. 9, 1 part of ipconazole, 35 parts of amixture (weight ratio 1:1) of white carbon and ammonium polyoxyethylenealkyl ether sulfate are mixed with an appropriate amount of water so asto give a total amount of 100 parts, and then the mixture isfinely-ground by a wet grinding method to obtain a flowable formulation.

Formulation Example 7

Ten (10) parts of the present carboxylic acid compound selected fromCompound No. 1 to Compound No. 9, 1 part of tebuconazole, 1.5 parts ofsorbitan trioleate, and 28 parts of an aqueous solution containing 2parts of polyvinyl alcohol are mixed, and then the mixture isfinely-ground by a wet grinding method. To this mixture is added anappropriate amount of an aqueous solution containing 0.05 parts ofxanthane gum and 0.1 parts of magnesium aluminium silicate so as to givea total amount of 90 parts, and then 10 parts of propylene glycol isadded thereto. The mixture is stirred to obtain a flowable formulation.

Formulation Example 8

Ten (10) parts of the present carboxylic acid compound selected fromCompound No. 1 to Compound No. 9, 1 part of difenoconazol, 1.5 parts ofsorbitan trioleate, and 28 parts of an aqueous solution containing 2parts of polyvinyl alcohol are mixed, and then the mixture isfinely-ground by a wet grinding method. To this mixture is added anappropriate amount of an aqueous solution containing 0.05 parts ofxanthane gum and 0.1 parts of magnesium aluminium silicate so as to givea total amount of 90 parts, and then 10 parts of propylene glycol isadded thereto. The mixture is stirred to obtain a flowable formulation.

Formulation Example 9

Ten (10) parts of the present carboxylic acid compound selected fromCompound No. 1 to Compound No. 9, 1 part of triadimenol, 1.5 parts ofsorbitan trioleate, and 28 parts of an aqueous solution containing 2parts of polyvinyl alcohol are mixed, and then the mixture isfinely-ground by a wet grinding method. To this mixture is added anappropriate amount of an aqueous solution containing 0.05 parts ofxanthane gum and 0.1 parts of magnesium aluminium silicate so as to givea total amount of 90 parts, and then 10 parts of propylene glycol isadded thereto. The mixture is stirred to obtain a flowable formulation.

Formulation Example 10

Ten (10) parts of the present carboxylic acid compound selected fromCompound No. 1 to Compound No. 9, 1 part of prothioconazole, 1.5 partsof sorbitan trioleate, and 28 parts of an aqueous solution containing 2parts of polyvinyl alcohol are mixed, and then the mixture isfinely-ground by a wet grinding method. To this mixture is added anappropriate amount of an aqueous solution containing 0.05 parts ofxanthane gum and 0.1 parts of magnesium aluminium silicate so as to givea total amount of 90 parts, and then 10 parts of propylene glycol isadded thereto. The mixture is stirred to obtain a flowable formulation.

Formulation Example 11

Ten (10) parts of the present carboxylic acid compound selected fromCompound No. 1 to Compound No. 9, 1 part of triticonazole, 1.5 parts ofsorbitan trioleate, and 28 parts of an aqueous solution containing 2parts of polyvinyl alcohol are mixed, and then the mixture isfinely-ground by a wet grinding method. To this mixture is added anappropriate amount of an aqueous solution containing 0.05 parts ofxanthane gum and 0.1 parts of magnesium aluminium silicate so as to givea total amount of 90 parts, and then 10 parts of propylene glycol isadded thereto. The mixture is stirred to obtain a flowable formulation.

Formulation Example 12

Ten (10) parts of the present carboxylic acid compound selected fromCompound No. 1 to Compound No. 9, 1 part of ipconazole, 1.5 parts ofsorbitan trioleate, and 28 parts of an aqueous solution containing 2parts of polyvinyl alcohol are mixed, and then the mixture isfinely-ground by a wet grinding method. To this mixture is added anappropriate amount of an aqueous solution containing 0.05 parts ofxanthane gum and 0.1 parts of magnesium aluminium silicate so as to givea total amount of 90 parts, and then 10 parts of propylene glycol isadded thereto. The mixture is stirred to obtain a flowable formulation.

Formulation Example 13

Ten (10) parts of the present carboxylic acid compound selected fromCompound No. 1 to Compound No. 9, 2 parts of tebuconazole, 3 parts ofcalcium lignin sulfonate, 2 parts of sodium lauryl sulfate, and the restparts of synthetic hydrated silicon oxide are well mixed while grindingto obtain 100 parts of a wettable powder.

Formulation Example 14

Ten (10) parts of the present carboxylic acid compound selected fromCompound No. 1 to Compound No. 9, 2 parts of difenoconazole, 3 parts ofcalcium lignin sulfonate, 2 parts of sodium lauryl sulfate, and the restparts of synthetic hydrated silicon oxide are well mixed while grindingto obtain 100 parts of a wettable powder.

Formulation Example 15

Ten (10) parts of the present carboxylic acid compound selected fromCompound No. 1 to Compound No. 9, 2 parts of triadimenol, 3 parts ofcalcium lignin sulfonate, 2 parts of sodium lauryl sulfate, and the restparts of synthetic hydrated silicon oxide are well mixed while grindingto obtain 100 parts of a wettable powder.

Formulation Example 16

Ten (10) parts of the present carboxylic acid compound selected fromCompound No. 1 to Compound No. 9, 2 parts of prothioconazole, 3 parts ofcalcium lignin sulfonate, 2 parts of sodium lauryl sulfate, and the restparts of synthetic hydrated silicon oxide are well mixed while grindingto obtain 100 parts of a wettable powder.

Formulation Example 17

Ten (10) parts of the present carboxylic acid compound selected fromCompound No. 1 to Compound No. 9, 2 parts of triticonazole, 3 parts ofcalcium lignin sulfonate, 2 parts of sodium lauryl sulfate, and the restparts of synthetic hydrated silicon oxide are well mixed while grindingto obtain 100 parts of a wettable powder.

Formulation Example 18

Ten (10) parts of the present carboxylic acid compound selected fromCompound No. 1 to Compound No. 9, 2 parts of ipconazole, 3 parts ofcalcium lignin sulfonate, 2 parts of sodium lauryl sulfate, and the restparts of synthetic hydrated silicon oxide are well mixed while grindingto obtain 100 parts of a wettable powder.

Formulation Example 19

Ten (10) parts of the present carboxylic acid compound selected fromCompound No. 1 to Compound No. 9, 1 part of metconazole, 35 parts of amixture (weight ratio 1:1) of white carbon and ammonium polyoxyethylenealkyl ether sulfate are mixed with an appropriate amount of water so asto give a total amount of 100 parts, and then the mixture isfinely-ground by a wet grinding method to obtain a flowable formulation.

Formulation Example 20

Ten (10) parts of the present carboxylic acid compound selected fromCompound No. 1 to Compound No. 9, 1 part of metconazole, 1.5 parts ofsorbitan trioleate, and 28 parts of an aqueous solution containing 2parts of polyvinyl alcohol are mixed, and then the mixture isfinely-ground by a wet grinding method. To this mixture is added anappropriate amount of an aqueous solution containing 0.05 parts ofxanthane gum and 0.1 parts of magnesium aluminium silicate so as to givea total amount of 90 parts, and then 10 parts of propylene glycol isadded thereto. The mixture is stirred to obtain a flowable formulation.

Formulation Example 21

Ten (10) parts of the present carboxylic acid compound selected fromCompound No. 1 to Compound No. 9, 2 parts of metconazole, 3 parts ofcalcium lignin sulfonate, 2 parts of sodium lauryl sulfate, and the restparts of synthetic hydrated silicon oxide are well mixed while grindingto obtain 100 parts of a wettable powder.

Treatment Example 1

The flowable formulation prepared in Formulation example 1 is used for asmear treatment in an amount of 500 ml per 100 kg of dried sorghum seedsby using a rotary seed treatment machine (seed dresser, produced byHans-Ulrich Hege GmbH) to obtain the treated seeds.

The seeds treated with each of the flowable formulations prepared inFormulation examples 2 to 12 are obtained in a manner similar to theabove, by using the flowable formulations prepared in Formulationexamples 2 to instead of the flowable formulation prepared inFormulation example 1.

Treatment Example 2

The flowable formulation prepared in Formulation example 1 is used for asmear treatment in an amount of 40 ml per 10 kg of dried corn seeds byusing a rotary seed treatment machine (seed dresser, produced byHans-Ulrich Hege GmbH) to obtain the treated seeds.

The seeds treated with each of the flowable formulations prepared inFormulation examples 2 to 12 are obtained in a manner similar to theabove, by using the flowable formulations prepared in Formulationexamples 2 to 12 instead of the flowable formulation prepared inFormulation example 1.

Treatment Example 3

The wettable powder prepared in Formulation example 13 is used forpowder coating treatment in an amount of 50 g per 10 kg of dried cornseeds to obtain the treated seeds.

The seeds treated with each of the wettable powders prepared inFormulation examples 14 to 18 are obtained in a manner similar to theabove, by using the wettable powders prepared in Formulation examples 14to 18 instead of the wettable powder prepared in Formulation example 13.

Treatment Example 4

The flowable formulation prepared in Formulation example 1 is used for asmear treatment in an amount of 50 ml per 10 kg of dried soybean seedsby using a rotary seed treatment machine (seed dresser, produced byHans-Ulrich Hege GmbH) to obtain the treated seeds.

The seeds treated with each of the flowable formulations prepared inFormulation examples 2 to 12 are obtained in a manner similar to theabove, by using the flowable formulations prepared in Formulationexamples 2 to instead of the flowable formulation prepared inFormulation example 1.

Next, the effect of the present invention is shown in Test examples.

Test Example 1

The present carboxylic acid compound (No. 3) 10 mg and tebuconazole ortriticonazole 1 mg are mixed, and thereto are added 150 microliters ofslurry that is prepared by mixing 10 parts of Color Coat Red(manufactured by Becker Underwood Inc.: coloring agent), 10 parts ofCF-CLEAR (manufactured by Becker Underwood Inc.: spreading agent) and anappropriate amount of water so as to give a total amount of 100 partsand the resulting mixture is then mixed thoroughly and 7.5 μL of themixture is added to 1 g of wheat seeds and the resulting mixture is thenagitated. After air drying, the treated wheat seeds are seeded into a 85mL plastic cup in a ratio of about 10 grains per the cup.

At 12 days post the seeding, spores of Puccinia recondita are inoculatedinto the cups, and then the cups are placed under a dark and humidcondition at 23° C. for 24 hours (hereinafter, referred to as a “treatedgroup”). At 7 days post the inoculation, a ratio of the symptom area ofthe second leaves to the total area of the second leaves is observed.

On the other hand, the same seeding and inoculation is carried out usingwheat seeds without the above-mentioned treatment (hereinafter, referredto as an “untreated group”), and at 7 days post the inoculation, a ratioof the symptom area of the second leaves to the total area of the secondleaves is observed.

From the results of the observation of the treated group and theuntreated group, a control effect in the treated group is calculated bythe following equation 1).

Control value (%)=(1−(Ratio of Symptom area of the second leaves toTotal area of the second leaves in Treated group)/(Ratio of Symptom areaof the second leaves to Total area of the second leaves in Untreatedgroup))×100  Equation 1):

The results show that an excellent control value is obtained in thetreated groups.

Test Example 2

The present carboxylic acid compound (No. 3) 10 mg and tebuconazole ortriticonazole 1 mg are mixed and thereto are added 150 microliters ofslurry that is prepared by mixing 10 parts of Color Coat Red(manufactured by Becker Underwood Inc.: coloring agent), 10 parts ofCF-CLEAR (manufactured by Becker Underwood Inc.: spreading agent) and anappropriate amount of water so as to give a total amount of 100 partsand the resulting mixture is then mixed thoroughly, and 37.5 μL of themixture is added to 5 g of corn seeds and the resulting mixture is thenagitated. After air drying, the treated corn seeds are seeded into a 300mL plastic cup in a ratio of 5 grains per the cup, and then covered withsoil which has been mixed with a wheat bran culture of Fusariumgraminearum (hereinafter, referred to as a “treated group”). At 18 dayspost the seeding, the number of seeds which fail to germinate isobserved.

On the other hand, the same seeding is carried out using corn seedswithout the above-mentioned treatment (hereinafter, referred to as an“untreated group”), and at 18 days post the seeding, the number of seedswhich fail to germinate is observed.

From the results of the observation of the treated group and theuntreated group, a control value is calculated by the following equation2).

Control value (%)=(1−(Ratio of seeds failed germinate to Total number ofsown seeds in Treated group)/(Ratio of seeds failed to germinate toTotal number of sown seeds in Untreated group))×100  Equation 2)

The results show that an excellent control value is obtained in thetreated groups.

Test Example 3

The present carboxylic acid compound (No. 1) or the present carboxylicacid compound (No. 4) 10 mg and tebuconazole or metconazole 1 mg weremixed, and thereto were added 150 microliters of slurry that wasprepared by mixing 10 parts of Color Coat Red (manufactured by BeckerUnderwood Inc.: coloring agent), 10 parts of CF-CLEAR (manufactured byBecker Underwood Inc.: spreading agent) and an appropriate amount ofwater so as to give a total amount of 100 parts and the resultingmixture was then mixed thoroughly and 7.5 μL of the mixture was added to1 g of wheat seeds and the resulting mixture was then agitated. Afterair drying, the treated wheat seeds were seeded into a 85 mL plastic cupin a ratio of about 10 grains per the cup.

At 12 days post the seeding, spores of Puccinia recondita wereinoculated into the cups, and then the cups were placed under a dark andhumid condition at 23° C. for 24 hours (hereinafter, referred to as a“treated group”). At 7 days post the inoculation, a ratio of the symptomarea of the second leaves to the total area of the second leaves wasobserved.

On the other hand, the same seeding and inoculation was carried outusing wheat seeds without the above-mentioned treatment (hereinafter,referred to as an “untreated group”), and at 7 days post theinoculation, a ratio of the symptom area of the second leaves to thetotal area of the second leaves was observed.

From the results of the observation of the treated group and theuntreated group, a control effect in the treated group was calculated bythe above equation 1). The two duplicate tests were performed. Theaverage value is shown in Table 2.

TABLE 2 Dose Control (g/100 kg value Test compounds of seeds) (%)Present compound 50 + 5 83 (Compound No. 1) + Tebuconazole Presentcompound 50 + 5 83 (Compound No. 4) + Tebuconazole Present compound 50 +5 92 (Compound No. 1) + Metconazole Present compound 50 + 5 92 (CompoundNo. 4) + Metconazole

Test Example 4

The present carboxylic acid compound (No. 4) 10 mg and tebuconazole ortriticonazole 1 mg were mixed and thereto were added 150 microliters ofslurry that was prepared by mixing 10 parts of Color Coat Red(manufactured by Becker Underwood Inc.: coloring agent), 10 parts ofCF-CLEAR (manufactured by Becker Underwood Inc.: spreading agent) and anappropriate amount of water so as to give a total amount of 100 partsand the resulting mixture was then mixed thoroughly, and 37.5 μL of themixture was added to 5 g of corn seeds and the resulting mixture wasthen agitated. After air drying, the treated corn seeds were seeded intoa 300 mL plastic cup in a ratio of 5 grains per the cup, and thencovered with soil which had been mixed with a wheat bran culture ofFusarium graminearum (hereinafter, referred to as a “treated group”). At18 days post the seeding, the number of seeds which failed to germinatewas observed.

On the other hand, the same seeding was carried out using corn seedswithout the above-mentioned treatment (hereinafter, referred to as an“untreated′group”), and at 18 days post the seeding, the number of seedswhich failed to germinate was observed.

From the results of the observation of the treated group and theuntreated group, a control value was calculated by the above equation2).

TABLE 3 Dose Control (g/100 kg value Test compounds of seeds) (%)Present compound 50 + 5 86 (Compound No. 4) + Tebuconazole Presentcompound 50 + 5 86 (Compound No. 4) + Triticonazole

Test Example 5

The present carboxylic acid compound (No. 1) 10 mg and tebuconazole,triticonazole or metconazole 1 mg were mixed and thereto were added 150microliters of slurry that was prepared by mixing 10 parts of Color CoatRed (manufactured by Becker Underwood Inc.: coloring agent), 10 parts ofCF-CLEAR (manufactured by Becker Underwood Inc.: spreading agent) and anappropriate amount of water so as to give a total amount of 100 partsand the resulting mixture was then mixed thoroughly, and 37.5 μL of themixture was added to 5 g of corn seeds and the resulting mixture wasthen agitated. After air drying, the treated corn seeds were seeded intoa 300 mL plastic cup in a ratio of 5 grains per the cup, and thencovered with soil which had been mixed with a wheat bran culture ofFusarium graminearum (hereinafter, referred to as a “treated group”). At18 days post the seeding, the number of seeds which failed to germinatewas observed.

On the other hand, the same seeding was carried out using corn seedswithout the above-mentioned treatment (hereinafter, referred to as an“untreated group”), and at 18 days post the seeding, the number of seedswhich failed to germinate was observed.

From the results of the observation of the treated group and theuntreated group, a control value was calculated by the above equation2).

TABLE 4 Dose Control (g/100 kg value Test compounds of seeds) (%)Present compound 50 + 5 83 (Compound No. 1) + Tebuconazole Presentcompound 50 + 5 83 (Compound No. 1) + Triticonazole Present compound50 + 5 83 (Compound No. 1) + Metconazole

1. A composition for controlling plant diseases comprising a carboxylicacid compound represented by a formula (I):

wherein n represents an integer selected from 1 to 5; R¹ represents ahalogen atom, a hydroxy group, a nitro group, a C1-C6 alkyl group or aC1-C6 alkoxy group; and when n represents an integer selected from 2 to5, each R¹ may be the same or different; or salts thereof and at leastone kind of azole compounds selected from the group (A) consisting oftebuconazole, difenoconazole, triticonazole, imazalil, triadimenol,fluquinconazole, prochloraz, prothioconazole, diniconazole, diniconazoleM, cyproconazole, tetraconazole, ipconazole, triforine, pyrifenox,fenarimol, nuarimol, oxpoconazole fumarate, pefurazoate, triflumizole,azaconazole, bitertanol, bromuconazole, epoxiconazole, fenbuconazole,flusilazole, flutriafol, hexaconazole, imibenconazole, myclobutanil,penconazole, propiconazole, simeconazole, triadimefon and metconazole.2. The composition for controlling plant diseases according to claim 1wherein a weight ratio of the carboxylic acid compound or salts thereofto the azole compounds is in the range of 100:1 to 1:100.
 3. Thecomposition for controlling plant diseases according to claim 1 whereinat least one kind of azole compounds is selected from the group (A)consisting of tebuconazole, difenoconazole, triticonazole, imazalil,triadimenol, fluquinconazole, prochloraz, prothioconazole, diniconazole,diniconazole M, cyproconazole, tetraconazole, ipconazole, triforine,pyrifenox, fenarimol, nuarimol, oxpoconazole fumarate, pefurazoate,triflumizole, azaconazole, bitertanol, bromuconazole, epoxiconazole,fenbuconazole, flusilazole, flutriafol, hexaconazole, imibenconazole,myclobutanil, penconazole, propiconazole, simeconazole and triadimefon.4. The composition for controlling plant diseases according to claim 3wherein a weight ratio of the carboxylic acid compound or salts thereofto the azole compounds is in the range of 100:1 to 1:100.
 5. A methodfor controlling plant diseases which comprises applying an effectiveamount of the composition for controlling plant diseases according toclaim 1 to a plant or a soil for cultivating the plant.
 6. A method forcontrolling plant diseases which comprises applying an effective amountof the composition for controlling plant diseases according to claim 1to plant seeds.
 7. The method for controlling plant diseases accordingto claim 6 wherein the plant seeds are seeds of corn, cotton, soybean,beet, rapeseed, wheat or rice.
 8. A method for controlling plantdiseases which comprises applying an effective amount of the compositionfor controlling plant diseases according to claim 3 to a plant or a soilfor cultivating the plant.
 9. A method for controlling plant diseaseswhich comprises applying an effective amount of the composition forcontrolling plant diseases according to claim 3 to plant seeds.
 10. Themethod for controlling plant diseases according to claim 9 wherein theplant seeds are seeds of corn, cotton, soybean, beet, rapeseed, wheat orrice.
 11. A method for controlling plant diseases which comprisesapplying an effective amount of the composition for controlling plantdiseases according to claim 2 to a plant or a soil for cultivating theplant.
 12. A method for controlling plant diseases which comprisesapplying an effective amount of the composition for controlling plantdiseases according to claim 2 to plant seeds.
 13. The method forcontrolling plant diseases according to claim 12 wherein the plant seedsare seeds of corn, cotton, soybean, beet, rapeseed, wheat or rice.
 14. Amethod for controlling plant diseases which comprises applying aneffective amount of the composition for controlling plant diseasesaccording to claim 4 to a plant or a soil for cultivating the plant. 15.A method for controlling plant diseases which comprises applying aneffective amount of the composition for controlling plant diseasesaccording to claim 4 to plant seeds.
 16. The method for controllingplant diseases according to claim 15 wherein the plant seeds are seedsof corn, cotton, soybean, beet, rapeseed, wheat or rice.